HCID 20242559, compound → 1-(3-Aminophenyl)-1,4-dihydroisoquinol-3-one

HRID 483142Notes

Reaction equation

HRID 483142 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12](=[O:20])[NH:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(OC(=O)C)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C:12](=[O:20])[NH:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 20242559HCID 20242559, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 202425531-(3-Aminophenyl)-1,4-dihydroisoquinol-3-oneYield 83.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3-nitrophenyl)-1,4-dihydroisoquinol-3-one (12.2 g) and 5% palladium-carbon (3 g) in ethylacetate (400 ml) was hydrogenated at room temperature and pressure until uptake of hydrogen ceased. The mixture was filtered (celite), and the filtrate evaporated to dryness to give 1-(3-aminophenyl)-1,4-dihydroisoquinol-3-one (9.0 g), m.p. 179°-180° C. which was used without purification.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered (celite)
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-623a79b470e9475c8df6cecbe27e1115
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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